Aromatic polyimides were well known as polymeric materials of high performance for their excellent thermal stabilities and balanced mechanical and electric properties. Polyimides were mainly used in the aerospace and electronic industries in the forms of films and moldings. Other uses for these polymers such as adhesives, gas separation membranes, composite matrices, coatings, and foams were rapidly increasing. However, aromatic polyimides are difficult to be processed because of high softening temperatures and limited solubilities in commercially available solvents; accordingly the improvements to their solubility and heat plasticity without decreasing their original excellent characteristics are the aims of the present researchers.
The literature is flooded with claims of polyimides according to our specific paper and patent search for soluble polyimides. Most of the literature described the improvement of diamines and relatively less literature described the invention of dianhydrides in the preparation of organosolubie polyimides. The diamines used in the synthesis of organosoluble polyimides have in general three kinds of structures. The first type is polyimides prepared from a polysiloxane diamine, which have an improved adhesion with a semiconductor substrate but suffer poorer thermal properties and strength of films. The second type is polyimides prepared from a diamine having two meta amino groups [such as, 3,3-diaminodiphenylsulfone and 1,3-bis(3-aminophenoxy)benzene], which have enhanced solubility but a lower degree of polymerization due to poor reactivity of the diamine. The third type is polyimides prepared from a diamine having two para amino groups, which will have organosolubility only when the diamines have more than one flexible connector groups selected from isopropyl, hexafluoroisopropyl, ether and sulfone [such as 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl ]hexafluoropropane, and bis[4-(4-aminophenoxy)phenyl]sulfone.
Our specific paper and patent search for organosoluble polyimides based on diamine are listed as follows:
(a) Patents
JP 09118,808 (1997) Chemical Abstract 127: 52287j EP 729,996 (1996) Chemical Abstract 125: 276948x U.S. Pat. No. 5,480,965 (1996) Chemical Abstract 124: 345157g JP 07-224,152 (1995) Chemical Abstract 124: 31222g JP 07-310,048 (1995) Chemical Abstract 124: 291209e EP 639,621 (1995) Chemical Abstract 123: 85015q JP 07-224,151 (1995) Chemical Abstract 123: 315836q JP 07-224,150 (1995) Chemical Abstract 123: 315835p JP 06-172,524 (1994) Chemical Abstract 121: 281875t JP 06-172,523 (1994) Chemical Abstract 121: 281874s JP 06-172,525 (1994) Chemical Abstract 121: 281876u U.S. Pat. No. 5,212,279 (1993) Chemical Abstract 119: 251699e JP 04-337,326 (1992) Chemical Abstract 119: 73356f JP 04-108,879 (1992) Chemical Abstract 117: 92386r JP 04-108,880 (1992) Chemical Abstract 117: 92387s EP 438,751 (1991) Chemical Abstract 115: 234851y U.S. Pat. No. 4,931,539 (1990) Chemical Abstract 113: 133121p JP 02-43,221 (1990) Chemical Abstract 113: 41153c JP 02-92,930 (1990) Chemical Abstract 113: 116471k JP 02-286,706 (1990) Chemical Abstract 115: 115256y EP 284,803 (1988) Chemical Abstract 110: 155428j JP 63-00,353 (1988) Chemical Abstract 109: 46242c JP 62-265,326 (1987) Chemical Abstract 108: 133522s JP 61-108,627 (1986) Chemical Abstract 106: 20093t JP 61-241,358 (1986) Chemical Abstract 106: 157082h JP 61-57,620 (1986) Chemical Abstract 105: 153750f JP 61-59,334 (1986) Chemical Abstract 105: 200510q EP 194,865 (1986) Chemical Abstract 105: 228674v JP 60-217,261 (1985) Chemical Abstract 104: 188323a JP 49-12,592 (1974) Chemical Abstract 83: 62006d JP 49-19,119 (1974) Chemical Abstract 82: 126002p JP 49-18,639 (1974) Chemical Abstract 82: 125993a JP 49-30,717 (1974) Chemical Abstract 82: 112854f JP 49-18,118 (1974) Chemical Abstract 82: 58904g JP 46-17,145 (1971) Chemical Abstract 75: 118915d Fr 1,539,074 (1968) Chemical Abstract 71: 4608t
(b) Articles
1. Arnold, C. A.; etc.; Polymer 30, 986 (1989). PA1 2. Omote, T.; etc.; Polym. Eng. Sci. 29, 945 (1989). PA1 3. Lee, H.-R; etc; Macromolecules. 23, 502 (1990). PA1 4. Arnold, F. E,; etc.; J. Mater. Chem. 3, 353 (1993). PA1 1. Yang C.-P; Lin J.-H, J. Polym. Sci., Part A:, 31, 2153 (1993). PA1 2. Yang C.-P; Chen W.-T, J. Polym. Sci., Part A:, 31, 2799 (1993). PA1 3. Yang C.-P; Chen W.-T, Macromol. Chem., 194, 3061 (1993). PA1 4. Yang C.-P; Chen W.-T, Macromolecules, 26, 4865 (1993). PA1 5. Yang C.-P; Lin J.-H, J. Polym. Sci., Part A:, 32, 423 (1994). PA1 6. Yang C.-P; Lin J.-H, J. Polym. Sci., Part A:, 32, 369 (1994). PA1 7. Hsiao S.-H; Yang C.-P; Fan J.-C, J. Polym. Res., 1, No. 4, 345 (1994). PA1 8. Hsiao S.-H; Yang C.-P; Lin C.-K, J. Polym. Res., 2, No. 1, 1 (1995). PA1 9. Yang C.-P; Hsiao S.-H; Jang C.-C, J. Polym. Sci., Part A:, 33, 1487 (1995). PA1 10. Yang C.-P; Lin J.-H, Polymer, 36, 2607 (1995). PA1 11. Yang C.-P; Lin J.-H, Polymeric Materials Encyclopedia, 9, 6214 (1996). PA1 12. Hsiao S.-H; Yang C.-P; Yang C.-Y, J. Polym. Sci., Part A:, 35, 1469 (1997). PA1 13. Liaw D.-J; Liaw B.-Y, Polym. J.,28, 970 (1996). PA1 Z=O, S, CH.sub.2, CO, SO.sub.2, C(Me).sub.2, C(CF.sub.3).sub.2, CR.sup.1 R.sup.2, X--C.sub.6 H.sub.4 --X, X--C.sub.10 H.sub.8 --X, X--C.sub.6 R.sup.1, R.sup.2, R.sup.3, R.sup.4 --X, or X--C.sub.6 H.sub.4 --Y--C.sub.6 H.sub.4 --X or a polysiloxane main chain;
Our specific paper and patent search for organosoluble polyimides based on diether-diamine:
The diamine, 1,4-bis(4-aminophenoxy)-2-tert-butylbenzene, was first disclosed in U.S. Pat. No. 5,085,676 (1992). The assignee of this U.S. patent, Du Pont Company, has claimed that the polyamides synthesized from this diamine, 1,4-bis(4-aminophenoxy)-2-tert-butylbenzene, possess a potential application as a gas separation membrane.